Any way to load these into Plex or do I have to use some sort of Apple software?

Yes and no.
If you're using a Mac, odds are you're not going to have a ton of luck, as most specific software designed to do this for Macs has quit working over the past few years (as I understand it, anyways)

If you're using Windows, you need to have iTunes <= 12.10.1.4 . If you do a bit of research, you can download 12.10.1.4 pretty easily. Some will say you need 12.9, but that shouldn't be necessary. As long as you completely deregister your computer with 12.10.1.4, you should be able to get it to work. Any higher and not so much.as Apple made some changes that companies are still trying to work around, as far as encryption. I'm not aware of any (yet) that have broken that.

Tuneskit, M4Vgear, there's a few other out there that work with 12.10.1.4 and lower though

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